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From Jon Lester to Mordecai Brown, the Cubs’ biggest moves at the Winter Meeting

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The rush of action caused by early roster deadlines has subsided. Since then, the Cubs have not participated in any early trades or signings. But fear not. The Winter Meeting is fast approaching.

Each year the Winter Conference ignites activity. Having all the team representatives under his one roof helps get things done. And for the first time since 2019, the Winter Meetings will be held in person starting Monday.

The Cubs have committed to being aggressive this offseason and have made some big moves before this time around.

Here’s a collection of the most significant moves the Cubs made during the Winter Conference: good, bad, recent and old.

Signed Jon Lester

The Cubs’ all-time free-agent signings came together during the 2014 Winter Conference. The club agreed a six-year, $155 million deal with Jon Lester, signing the deal just days later.

In retrospect, the acquisition of Leicester was what propelled the Cubs to five playoff appearances in six years, including three consecutive National League Championship Series and World Series wins. . However, Kyle Hendricks, the last Cub left on that title team, said at the time he felt Leicester’s arrival was a turning point.

“You knew when it happened in the offseason,” Hendricks recently told The Sun-Times. “Maybe I never thought about it, but I knew. This is the team that has it all now. We’re going somewhere. We’re winning.” .”

they won. Lester posted a 3.64 ERA and a .636 winning percentage during his Chicago days, earning him two All-Star selections and placing him second in his NL Cy Young voting as a Cub.

Trading with Mordecai Brown

From the recent winter meeting to the early iterations: Hall of Famer Mordecai Brown’s landing on the Cubs began in December 1903 with the National League. Sabr.org.

Only half of “The Sporting News” reports came to fruition. The Cubs sent Taylor and catcher Larry McLean to St. Louis for Brown and catcher Jack O’Neill. Thus, the pitcher nicknamed “Three Fingers” began a nine-year run in Chicago.

Brown made his third consecutive World Series appearance with the Cubs, winning two of them.

Lee Smith traded to Red Sox

The Cubs didn’t just make deals to trade future Hall of Famers at the Winter Games. They sent them away too. Cue 1987.

The Cubs traded Lee Smith to the Red Sox for pitchers Al Nipper and Calvin Shiraldi.

Drafted by the Cubs in 1975, Smith was already a two-time All-Star. He also earned his five All-Star selections, and in that illustrious career he won his three Rolaids Relief Man Awards.

Nipper has appeared in just 22 games for the Cubs. Ciraldi posted a 4.19 ERA in his two part of his season with the team.

Contract with Ben Zobrist

With Ben Zobrist, the Cubs won utility player, 2016 All-Star, and postseason hero. They’ve secured the man with the biggest hits in Cubs history.

Zobrist famously drove in the 10th-inning go-ahead run in Game 7 of the World Series and hit an opposite-field double in the Cubs’ curse-breaking victory. He was named MVP of the series.

Zobrist’s tenure with the Cubs began with the signing of the Winter Meeting in 2015. He signed his $56 million contract over his four years.

Bruce Sutter traded to Cardinals

Hall of Famer Bruce Sutter’s career was split primarily between the Cubs and rival Cardinals. That switch between teams was due to a trade in his meeting with Winter in 1980. Sutter was traded to St. Louis for outfielder Leon Durham, third baseman Ken Hereitz, and utility tie his player Waller (a player who would later be named).

Sutter had won the NL Cy Young Award two seasons ago and was named an All-Star four years in a row. But before trading Sutter, the Cubs tried to downplay him in arbitration.

They lost, and Sutter received $700,000 in what would be his final year with the Cubs when he was offered $350,000.

Durham was named an All-Star twice in his seven-and-a-half seasons with the Cubs. Reitz and Waller’s tenures were shorter. Sutter’s departure at least made room for Smith to take over closer.

Sutter added two more All-Star selections to his resume with the Cardinals.

Contract with Ted Lilly

Lefty Ted Lilly was an All-Star and led the league in his 2008 start, posting a 3.70 ERA with the Cubs. But his 2006 signing also became part of the Cubs’ Winter Meeting lore.

In 2006, General Manager Jim Hendry was hospitalized for angioplasty. But he kept working.

“Jim was hooked up to an ECG machine, and we went through with it,” Lilly’s agent Larry O’Brien told reporters at the time.

As a result of Hendry’s efforts, Lilly signed a four-year, $40 million deal.


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Written by Natalia Chi

Chicago Popular; Chicago breaking news, weather and live video. Covering local politics, health, traffic and sports for Chicago, the suburbs and northwest Indiana.

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